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361.
Maurizio Chiminelli Dr. Andrea Serafino Davide Ruggeri Prof. Luciano Marchiò Prof. Franca Bigi Prof. Raimondo Maggi Prof. Max Malacria Prof. Giovanni Maestri 《Angewandte Chemie (International ed. in English)》2023,62(12):e202216817
Dearomative cycloadditions are a powerful tool to access a large chemical space exploiting simple and ubiquitous building blocks. The energetic burden due to the loss of aromaticity has however greatly limited their synthetic potential. We devised a general intramolecular method that overcomes these limitations thanks to the photosensitization of allenamides. The visible-light-promoted process gives complex [2.2.2]-(hetero)-bicyclooctadienes at room temperature, likely through the stabilization of transient (bi)radicals by naphthalene. The reaction tolerates several valuable functionalities, offering a convenient handle for a myriad of applications, including original isoindoles and metal complexes. 相似文献
362.
Manuel Weh Dr. Asja A. Kroeger Dr. Kazutaka Shoyama Dr. Matthias Grüne Prof. Amir Karton Prof. Dr. Frank Würthner 《Angewandte Chemie (International ed. in English)》2023,62(19):e202301301
Enzymes actuate catalysis through a combination of transition state stabilization and ground state destabilization, inducing enantioselectivity through chiral binding sites. Here, we present a supramolecular model system which employs these basic principles to catalyze the enantiomerization of [5]helicene. Catalysis is hereby mediated not through a network of functional groups but through π-π catalysis exerted from the curved aromatic framework of a chiral perylene bisimide (PBI) cyclophane offering a binding pocket that is intricately complementary with the enantiomerization transition structure. Although transition state stabilization originates simply from dispersion and electrostatic interactions, enantiomerization kinetics are accelerated by a factor of ca. 700 at 295 K. Comparison with the meso-congener of the catalytically active cyclophane shows that upon configurational inversion in only one PBI moiety the catalytic effect is lost, highlighting the importance of precise transition structure recognition in supramolecular enzyme mimics. 相似文献
363.